Outremont is the town that stayed a town. It was its own city until 2002, and it still carries itself like one — leafy, well-off, turned slightly away from the rest of Montreal, with shopping streets that feel borrowed from a small French provincial centre rather than a North American metropolis.
About four kilometres, best in the morning when the avenues are quiet and the patisseries are warm. Start on Avenue Bernard with its wide median and its terraces, then drift one block to Avenue Laurier — the cheese shops, the bookshop windows, the bourgeois high street doing exactly what it was built to do. Cut up to Parc Outremont, a formal pond ringed by the hill's grandest houses, and keep climbing past the gabled stone mansions where the lots only get larger.
Then come down the lower slope, where Outremont's Hasidic families live around Hutchison and Saint-Viateur — a neighbourhood at home, to be walked quietly. End at the Mile End line, where the bagel ovens are a block away and the metro is close.
